Hydrochloric Acid → 2-(3',5'-Dimethoxy-4'-hydroxy-phenyl)-indole

HRID 65855Notes

Reaction equation

HRID 65855 reaction equation
O.[OH-].[Na+].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:24]2[NH:25][C:26]3[C:31]([CH:32]=2)=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:9]=[C:10]([O:22][CH3:23])[C:11]=1[O:12]S(C1C=CC=CC=1)(=O)=O.Cl>CO>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:24]2[NH:25][C:26]3[C:31]([CH:32]=2)=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:9]=[C:10]([O:22][CH3:23])[C:11]=1[OH:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 227561262-(3',5'-Dimethoxy-4'-benzenesulphonyloxy-phenyl)-indole

Product 1

HCID 227520162-(3',5'-Dimethoxy-4'-hydroxy-phenyl)-indoleYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a reactor were introduced 10 ml of water containing 4.8g of solid sodium hydroxide, 30 ml of methanol and 75.6g (0.02 mol) of 2-(3',5'-dimethoxy-4'-benzenesulphonyloxy-phenyl)-indole. The reaction medium was heated to 50°-55° C., was stirred for 1 hour and was poured into an aqueous solution of hydrochloric acid. The indole derivative was extracted with ether and the ethereal phase was washed with water to neutrality, dried, treated with charcoal and, finally concentrated under reduced pressure to give 2-(3',5'-dimethoxy-4'-hydroxy-phenyl)-indole which was recrystallized from a mixture of ethanol-acetone 60/40.

Workup

  1. temperatureThe reaction medium was heated to 50°-55° C.
  2. extractionThe indole derivative was extracted with ether
  3. washthe ethereal phase was washed with water to neutrality
  4. customdried
  5. additiontreated with charcoal
  6. concentrationfinally concentrated under reduced pressure

Sources & evidence

ORD record
ord-1804f64c69a447309bc69c42b5af627f
Source dataset
uspto-grants-1978_12
Patent number
US04129572

Reaction notes

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